Robinson annulation reaction
E545316
The Robinson annulation reaction is a classic organic chemistry transformation that forms six-membered rings by combining a Michael addition with an intramolecular aldol condensation, widely used in the synthesis of complex cyclic molecules and natural products.
All labels observed (2)
| Label | Occurrences |
|---|---|
| Robinson annulation reaction canonical | 1 |
| Robinson–Schöpf reaction | 1 |
How this entity was disambiguated
This entity first appeared as the object of triple T5781890 — resolving that mention is where its identity was fixed. The disambiguator weighed these candidate entities and picked the highlighted one (or “None”, minting a new entity). This is how homonymy is resolved: the same surface form can point to different entities.
NED1
Entity disambiguation (via context triple)
gpt-5-mini-2025-08-07
Target entity: Robinson annulation reaction Context triple: [Robert Robinson, knownFor, Robinson annulation reaction]
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A.
Barton reaction
The Barton reaction is an organic photochemical transformation that converts nitrite esters into δ-nitroso alcohols via intramolecular hydrogen abstraction and radical rearrangement.
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B.
Eschenmoser sulfide contraction
Eschenmoser sulfide contraction is an organic rearrangement reaction that converts certain sulfur-containing intermediates into carbonyl compounds, widely used in complex molecule and natural product synthesis.
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C.
Suzuki coupling
Suzuki coupling is a widely used palladium-catalyzed cross-coupling reaction that forms carbon–carbon bonds between organoboron compounds and organic halides, fundamental in organic synthesis and pharmaceutical chemistry.
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D.
Buchwald–Hartwig amination
The Buchwald–Hartwig amination is a palladium-catalyzed cross-coupling reaction that forms carbon–nitrogen bonds by coupling aryl (or vinyl) halides with amines, widely used in the synthesis of pharmaceuticals and fine chemicals.
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E.
Eschenmoser–Claisen rearrangement
The Eschenmoser–Claisen rearrangement is a variant of the Claisen rearrangement in organic chemistry that converts allylic alcohols and amides into γ,δ-unsaturated carbonyl compounds via a [3,3]-sigmatropic rearrangement.
- F. None of above. chosen
- G. Unsure - the case is ambiguous/there is not enough information to decide.
NED2
Entity disambiguation (via description)
gpt-5-mini-2025-08-07
Target entity: Robinson annulation reaction Target entity description: The Robinson annulation reaction is a classic organic chemistry transformation that forms six-membered rings by combining a Michael addition with an intramolecular aldol condensation, widely used in the synthesis of complex cyclic molecules and natural products.
-
A.
Barton reaction
The Barton reaction is an organic photochemical transformation that converts nitrite esters into δ-nitroso alcohols via intramolecular hydrogen abstraction and radical rearrangement.
-
B.
Eschenmoser sulfide contraction
Eschenmoser sulfide contraction is an organic rearrangement reaction that converts certain sulfur-containing intermediates into carbonyl compounds, widely used in complex molecule and natural product synthesis.
-
C.
Suzuki coupling
Suzuki coupling is a widely used palladium-catalyzed cross-coupling reaction that forms carbon–carbon bonds between organoboron compounds and organic halides, fundamental in organic synthesis and pharmaceutical chemistry.
-
D.
Buchwald–Hartwig amination
The Buchwald–Hartwig amination is a palladium-catalyzed cross-coupling reaction that forms carbon–nitrogen bonds by coupling aryl (or vinyl) halides with amines, widely used in the synthesis of pharmaceuticals and fine chemicals.
-
E.
Eschenmoser–Claisen rearrangement
The Eschenmoser–Claisen rearrangement is a variant of the Claisen rearrangement in organic chemistry that converts allylic alcohols and amides into γ,δ-unsaturated carbonyl compounds via a [3,3]-sigmatropic rearrangement.
- F. None of above. chosen
Statements (47)
| Predicate | Object |
|---|---|
| instanceOf |
annulation reaction
ⓘ
carbon–carbon bond-forming reaction ⓘ name reaction ⓘ organic reaction ⓘ |
| appearsIn | organic chemistry textbooks ⓘ |
| category |
carbonyl chemistry
ⓘ
pericyclic-related transformations ⓘ |
| combines |
Michael addition
ⓘ
intramolecular aldol condensation ⓘ |
| developedIn | 20th century ⓘ |
| forms | C–C bonds ⓘ |
| importantFor | asymmetric synthesis ⓘ |
| mechanisticStep |
1,4-conjugate addition
ⓘ
dehydration ⓘ enolate formation ⓘ intramolecular aldol addition ⓘ |
| namedAfter | Robert Robinson ⓘ |
| productFeature |
conjugated enone system
ⓘ
ring formation ⓘ |
| reactionType | conjugate addition–condensation sequence ⓘ |
| relatedTo |
Dieckmann condensation
ⓘ
Michael reaction ⓘ aldol reaction ⓘ |
| requires | base ⓘ |
| ringSize | six-membered ring ⓘ |
| stereochemicalOutcome | creates stereocenters ⓘ |
| taughtIn | advanced organic chemistry courses ⓘ |
| typicalBase |
alkoxide base
ⓘ
hydroxide base ⓘ |
| typicalElectrophile |
enone
ⓘ
α,β-unsaturated carbonyl compound ⓘ |
| typicalNucleophile |
enolate
ⓘ
ketone enolate ⓘ |
| typicalProduct |
cyclohexenone
ⓘ
six-membered carbocycle ⓘ |
| typicalSolvent |
alcohol solvent
ⓘ
ethanol ⓘ |
| typicalSubstrate |
1,3-dicarbonyl compound
ⓘ
cyclic ketone ⓘ methyl vinyl ketone ⓘ |
| usedFor |
construction of bicyclic systems
ⓘ
construction of polycyclic frameworks ⓘ construction of tricyclic systems ⓘ |
| usedIn |
natural product synthesis
ⓘ
steroid synthesis ⓘ synthesis of complex cyclic molecules ⓘ total synthesis ⓘ |
How these facts were elicited
The pipeline generated the facts above by prompting gpt-5.1 with this entity's name + description and the instruction below.
Instruction
You are a knowledge base construction expert. Given a subject entity and a description of it, return factual statements that you know for the subject as a JSON list of dictionaries(triples), where keys must be "subject", "predicate" and "object". The number of facts may be very high, between 25 to 50 or more, for very popular subjects. For less popular subjects, the number of facts can be very low, like 5 or 10. # Requirements - If you don't know the subject at all, return an empty list. - If the subject is not a named entity, return an empty list. - Include at least one triple where predicate is "instanceOf". - Do not get too wordy. - Separate several objects into multiple triples with one object.
Input
Subject: Robinson annulation reaction Description of subject: The Robinson annulation reaction is a classic organic chemistry transformation that forms six-membered rings by combining a Michael addition with an intramolecular aldol condensation, widely used in the synthesis of complex cyclic molecules and natural products.
Referenced by (2)
Full triples — surface form annotated when it differs from this entity's canonical label.
linked to: Robinson annulation reaction